Phosphate → (2R,3S)-3-Phenoxyacetylamino-2-[(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester

HRID 345631

반응식

HRID 345631 반응식
C(O)(=O)C(O)=O.[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][CH2:13][CH:14]1[CH2:17][C:16](=[O:18])[N:15]1[CH2:19][C:20]([O:22][CH3:23])=[O:21].[O:24]([CH2:31][C:32]([O:34]C)=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[OH-].[K+].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)[N:46]2[C@H]1C(O)=O>O>[O:24]([CH2:31][C:32]([NH:46][C@@H:17]1[C:16](=[O:18])[N:15]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C@@H:14]1[CH2:13][CH2:12][C:8]1[O:7][CH:11]=[CH:10][CH:9]=1)=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 5

HCID 1061PhosphateHCID 5904Penicillin GHCID 14797Potassium HydroxideHCID 16365Methyl phenoxyacetateHCID 86745171HCID 86745171, 화합물

생성물 1

HCID 9886466(2R,3S)-3-Phenoxyacetylamino-2-[(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester수율 13%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
28 °C

실험 절차

A 100 mg sample of [(2R,3S),(2S,3R)]-3-amino- <2-[2-(2-furanyl)ethyl]-4-oxo-1-azetidine acetic acid, methyl ester oxalate salt and a 135 mg sample of methyl phenoxyacetate were added to 0.lM phosphate buffer (100 ml final volume) and adjusted to pH=6.0 with lN KOH. Milli-Q™ H2O washed Sclavo penicillin G amidase (40 I.U. of enzyme per gram of substrate) was then added to the reaction mixture and the pH of reaction mixture was maintained at 6.0 and temperature at 28° C. for 8 hours. The reaction mixture was then filtered to remove the immobilized enzyme and extracted two times with ethyl acetate. The organic extracts were then dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The title compound was then isolated by column chromatography from this residue using a Kiesegel 60™ column eluted with toluene/ethyl acetate (70/30). Yield: 13%.

후처리

  1. customthe pH of reaction mixture
  2. filtrationThe reaction mixture was then filtered
  3. customto remove the immobilized enzyme
  4. extractionextracted two times with ethyl acetate
  5. dry with materialThe organic extracts were then dried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-678c2905b4724c37ac1f44b76fa1f741
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057607

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